CN113004277B - Naphthalimide compound and preparation method and application thereof - Google Patents
Naphthalimide compound and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to naphthalimide compounds and a preparation method and application thereof, wherein the structure of the naphthalimide compounds is shown as a formula (I), wherein R is1Is selected from C4‑8Chain alkyl radical, C5‑7A cycloalkyl group; r2Selected from phenyl and 5-7 membered aromatic heterocyclic radical. The naphthalimide compound related by the invention is a naphthalimide compound with a novel structure, can generate a large amount of free radicals under the condition of illumination and has photochromic property; and the synthesis is simple, the preparation cost is low, and the method can be widely applied to preparation of photochromic materials.
Description
Technical Field
The invention belongs to the technical field of photochromic materials, relates to a naphthalimide compound, a preparation method and application thereof, and particularly relates to a naphthalimide compound, a preparation method thereof and application thereof in preparing a photochromic material with simple synthesis and low cost.
Background
Compared with inorganic photochromic materials, organic photochromic materials are widely researched due to the characteristics of high response speed, easy processing and the like, and are applied to the fields of photochromic lenses, optical information recording materials, molecular leads, molecular switches and the like.
The color change mechanism of the organic photochromic material is as follows: 1. certain changes in the structure of organic molecules (chemical bond dissociation, heterolysis/photocyclization, cis-trans isomerization, protonation or deprotonation processes, etc.); 2. a redox active organic molecule (e.g., viologen derivative).
CN111606915A discloses a preparation method of a spiropyran photochromic material, which comprises the following steps: 2,3, 3-trimethyl-3H-indole compounds are used as an initiator, methanol is used as an alkylating reagent, alkylation reaction is carried out at room temperature in the presence of sulfuryl fluoride atmosphere, an acid-binding agent and an organic solvent, after the reaction is finished, salicylaldehyde and ethanol are added into the system, heating is carried out until reflux reaction is carried out, and the reaction product is separated and purified to obtain the spiropyran photochromic material. The sulfuryl fluoride atmosphere is used in the synthesis process of the material, so that the material has very high raw material cost and process cost, and large-scale application is difficult to realize.
CN111808120A discloses a colorless to blue spirooxazine photochromic compound, a preparation method and an application thereof, the colorless to blue spirooxazine photochromic compound prepared by the invention has the advantages of high photoresponse speed, rapid fading, stable performance when the closed-loop state is used outdoors, no precious metal, low activity of nano enzyme and weak antibacterial performance. And the synthesis is complex, 4-5 steps of organic reaction are needed, the total yield is not high, and the raw material price is high.
Therefore, the development of a photochromic material which is simple to synthesize and low in cost is an urgent problem to be solved in the field.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a naphthalimide compound and a preparation method and application thereof, in particular to a naphthalimide compound and a preparation method and application thereof in preparing a photochromic material with simple synthesis and low cost.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a naphthalimide compound, which has a structure represented by formula (i):
wherein R is1Is selected from C4-8Chain alkyl radical, C5-7A cycloalkyl group; r2Selected from phenyl and 5-7 membered aromatic heterocyclic radical.
Said C is4-8The alkyl group means an acyclic alkyl group having 4 to 8 carbon atoms, such as a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group; said C is5-7Cycloalkyl means a cycloalkyl group having 5 to 7 carbon atoms, such as cyclopentyl, cyclohexyl, cycloheptyl; the 5-to 7-membered aromatic heterocyclic group is exemplified by a 5-membered aromatic heterocyclic group, a 6-membered aromatic heterocyclic group, a 7-membered aromatic heterocyclic group.
The naphthalimide compound related by the invention is a naphthalimide compound with a novel structure, can generate a large amount of free radicals under the condition of illumination and has photochromic property; and the synthesis is simple, the preparation cost is low, and the method can be widely applied to preparation of photochromic materials.
Preferably, in formula (I), R1Selected from butyl, pentyl, hexyl, cyclohexyl; r2Selected from phenyl and pyridyl.
When R is1Selected from butyl, pentyl, hexyl, cyclohexyl, R2When the compound is selected from phenyl and pyridyl, the naphthalimide compound according to the present invention has more excellent photochromic properties.
In a second aspect, the present invention provides a method for preparing the naphthalimide compound according to the first aspect, comprising the steps of:
under the protection of protective gas, 1,4,5, 8-naphthalene tetracarboxylic anhydride and R1-NH2、R2-NH2Mixing the raw materials in an organic solvent, and reacting to obtain the naphthalimide compound; r1、R2Is in accordance with the scope of the first aspect.
The reaction formula is shown as follows:
the preparation method of the naphthalimide compound is simple and easy to operate, is very suitable for industrial large-scale production, and has practicability.
Preferably, the organic solvent includes any one of ethanol, methanol, N-dimethylformamide, N-dimethylacetamide, or N-methylpyrrolidone, or a combination of at least two thereof.
The combination of at least two of the above-mentioned compounds, for example, the combination of ethanol and methanol, the combination of N, N-dimethylformamide and N, N-dimethylacetamide, the combination of N, N-dimethylacetamide and N-methylpyrrolidone, and the like, can be selected in any combination manner, and are not described in detail herein.
Preferably, said R is1-NH2And R2-NH2The molar ratio of (a) to (b) is 1:2 to 2:1, for example, 1:2, 2:3, 1:1, 3:2, 2:1, etc., and other specific values within the numerical range can be selected, which is not described herein again.
Preferably, said R is1-NH2And R2-NH2The total molar amount of the naphthalene tetracarboxylic anhydride is 1-5 times, such as 1 time, 2 times, 3 times, 4 times, 5 times and the like, and other specific values in the numerical range can be selected, which is not repeated herein.
Preferably, the reaction temperature is 90-150 ℃, such as 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃ and the like, and the time is 12-48h, such as 12h, 20h, 24h, 30h, 36h, 42h, 46h, 48h and the like, and other specific values in the numerical range can be selected, and are not repeated herein.
Preferably, after the reaction is complete, the product is cooled, poured into water, then filtered and purified by column chromatography.
Preferably, the column chromatography is a silica gel column and the mobile phase is dichloromethane and/or chloroform.
In a third aspect, the present invention provides a naphthalimide-based photochromic material, the raw material for preparing the naphthalimide-based photochromic material comprises the naphthalimide-based compound according to the first aspect.
In a fourth aspect, the present invention provides a use of the naphthalimide compound according to the first aspect in the preparation of a photochromic material.
Compared with the prior art, the invention has the following beneficial effects:
the naphthalimide compound related by the invention is a naphthalimide compound with a novel structure, can generate a large amount of free radicals under the condition of illumination and has photochromic property; and the synthesis is simple, the preparation cost is low, and the method can be widely applied to preparation of photochromic materials.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a naphthalimide compound obtained in example 1;
FIG. 2 is a nuclear magnetic carbon spectrum of the naphthalimide compound obtained in example 1;
FIG. 3 is a nuclear magnetic hydrogen spectrum of the naphthalimide compound obtained in example 2;
FIG. 4 is a nuclear magnetic carbon spectrum of the naphthalimide compound obtained in example 2;
FIG. 5 is a nuclear magnetic hydrogen spectrum of the naphthalimide compound obtained in example 3;
FIG. 6 is a nuclear magnetic carbon spectrum of the naphthalimide compound obtained in example 3;
FIG. 7 is a graph showing a UV-VIS absorption spectrum of the naphthalimide-based compound obtained in example 1;
FIG. 8 is a graph showing an ultraviolet-visible absorption spectrum of a naphthoylimine compound obtained in example 2;
FIG. 9 is a graph showing a UV-VIS absorption spectrum of a naphthalimide-based compound obtained in example 3;
FIG. 10 is an electron paramagnetic spectrum of the naphthalimide-based compound obtained in example 1;
FIG. 11 is an electron paramagnetic spectrum of the naphthalimide compound obtained in example 2;
FIG. 12 is an electron paramagnetic spectrum of the naphthalimide compound obtained in example 3;
FIG. 13 is a front and rear appearance view of the naphthalimide-based compound obtained in example 1 under light irradiation;
FIG. 14 is a front and rear view of the naphthalimide-based compound obtained in example 2 under light irradiation;
FIG. 15 is a front and rear external view of the naphthalimide-based compound obtained in example 3 under light irradiation.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
This example prepares a naphthalimide compound of the structure:
the preparation method comprises the following steps:
dissolving 1,4,5, 8-naphthalene tetracarboxylic anhydride (1.41g, 5.26mmol) in 50mL of N, N-dimethylformamide, adding cyclohexylamine (0.52g, 5.26mmol)) and aniline (0.49g, 5.26mmol), heating to 150 ℃, and keeping the temperature constant for 24 h; and cooling the reaction liquid to 20 ℃, pouring into 500mL of water, filtering, and performing column chromatography on a filter cake (a stationary phase is silica gel, and dichloromethane is a mobile phase) to obtain the naphthalimide compound.
The nuclear magnetic hydrogen spectrogram and the carbon spectrogram of the naphthalimide compound are respectively shown as figure 1 and figure 2, and the specific chemical shift is as follows:1H NMR(400MHz,CDCl3)δ＝8.82-8.75(m,4H),7.62-7.56(m,2H),7.56-7.50(m,1H),7.36-7.31(m,2H),5.04(tt,J＝12.2,3.7Hz,1H),2.54(qd,J＝12.4,3.5Hz,2H),1.93(d,J＝12.9Hz,2H),1.83-1.71(m,3H),1.55-1.41(m,2H),1.41-1.30(m,1H)。
13C NMR(101MHz,CDCl3)δ＝163.17,163.10,134.57,131.38,130.93,129.60,129.20,128.42,127.48,126.92,126.79,126.35,54.51,29.05,26.45,25.31。
example 2
This example prepares a naphthalimide compound of the structure:
the preparation method comprises the following steps:
dissolving 1,4,5, 8-naphthalene tetracarboxylic anhydride (1.41g, 5.26mmol) in 50mL of N, N-dimethylformamide, adding cyclohexylamine (0.52g, 5.26mmol) and 4-aminopyridine (0.50g, 5.26mmol), heating to 130 ℃ and keeping the temperature for 36 h; and cooling the reaction liquid to 20 ℃, pouring into 500mL of water, filtering, and performing column chromatography on filter cakes (the stationary phase is silica gel and the trichloromethane is a mobile phase) to obtain the naphthalimide compound.
The nuclear magnetic hydrogen spectrogram and the carbon spectrogram of the naphthalimide compound are respectively shown as fig. 3 and fig. 4, and the specific chemical shifts are as follows:1H NMR(400MHz,CDCl3)δ＝8.87(d,J＝6.3Hz,2H),8.83-8.76(m,4H),7.40(d,J＝5.8Hz,2H),5.03(tt,J＝12.3,3.7Hz,1H),2.63-2.41(m,2H),1.87-1.70(m,4H),1.53-1.21(m,4H)。
13C NMR(101MHz,CDCl3)δ＝162.98,162.36,151.13,142.66,131.64,130.96,127.87,126.83,125.83,123.91,54.66,29.09,26.47,25.32。
example 3
This example prepares a naphthalimide compound of the structure:
the preparation method comprises the following steps:
1,4,5, 8-naphthalene tetracarboxylic anhydride (1.41g, 5.26mmol) is dissolved in 50mL ethanol, cyclohexylamine (0.52g, 5.26mmol)) and 3-aminopyridine (0.50g, 5.26mmol) are added, and the mixture is heated to 110 ℃ and kept at the constant temperature for 48 h; and cooling the reaction liquid to 20 ℃, pouring into 500mL of water, filtering, and performing column chromatography on filter cakes (the stationary phase is silica gel and the trichloromethane is a mobile phase) to obtain the naphthalimide compound.
The nuclear magnetic hydrogen spectrogram and the carbon spectrogram of the naphthalimide compound are respectively shown as fig. 5 and fig. 6, and the specific chemical shifts are as follows:1H NMR(400MHz,DMSO-d6)δ8.84-8.53(m,7H),7.94(dt,J＝8.1,1.7Hz,2H),7.64(dd,J＝8.0,4.8Hz,1H),5.00-4.79(m,1H),2.47-2.35(m,2H),1.92-1.74(m,3H),1.71(d,J＝12.1Hz,1H),1.47-1.32(m,2H),1.30-1.20(m,1H)。
13C NMR(101MHz,DMSO)δ163.38,150.21,149.88,137.42,132.79,131.02,130.85,127.49,126.88,126.81,126.64,124.52,53.94,29.05,26.55,25.67。
test example 1
The naphthalimide compounds prepared in examples 1 to 3 were subjected to in-situ solid uv-vis absorption spectroscopy detection (irradiation of blue light (wavelength 460 to 465 nm)) by using a uv-vis spectrometer (PE 800-S), and tested before and at different times of irradiation.
The obtained UV-visible absorption spectra are shown in FIGS. 7-9, respectively, and it can be seen that no new absorption band appears after the sample is irradiated by blue light (with a wavelength of 460-465 nm) compared with the sample before being irradiated by light, but the absorption band at 450-800 nm is significantly enhanced. In addition, the absorption band shows a gradually increasing trend with the increase of the illumination time.
Test example 2
An electron paramagnetic resonance spectrometer (Bruk Bio-Spin E500) is used to test the electron paramagnetic spectra of the naphthalimide compounds prepared in examples 1-3 before illumination and after illumination time of 180s (blue light (wavelength is 460-465 nm) illumination).
The electron paramagnetic spectra are shown in FIGS. 10 to 12, respectively, and it is understood from these graphs that the same conclusion as in test example 1 can be obtained. Specifically, a strong radical signal was detected at g-2.004 before the sample was not illuminated, forming a stable organic radical anion. After illumination, the signal at g-2.004 is obviously enhanced, and the concentration of free radicals in the material is increased along with illumination.
Test example 3
The naphthalimide compounds prepared in examples 1 to 3 were observed for discoloration before light irradiation and after light irradiation for 180 seconds (blue light (wavelength of 460 to 465 nm)) and the comparative figures are shown in fig. 13 to 15, respectively, which shows that the naphthalimide compounds according to the present invention have significant photochromic properties.
The applicant states that the present invention is illustrated by the above examples to show a naphthalimide compound of the present invention, a preparation method and applications thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
Claims (9)
1. A naphthalimide compound is characterized in that the structure of the naphthalimide compound is shown as the formula (I):
wherein R is1Is selected from cyclohexyl; r2Selected from phenyl and pyridyl.
2. The method of claim 1, wherein the method comprises the steps of:
under the protection of protective gas, 1,4,5, 8-naphthalene tetracarboxylic anhydride and R1-NH2、R2-NH2Mixing the raw materials in an organic solvent, and reacting to obtain the naphthalimide compound; r1、R2Is in accordance with the definition in claim 1;
the organic solvent comprises any one or the combination of at least two of ethanol, methanol, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
3. The method of claim 2, wherein R is naphthalene imide1-NH2And R2-NH2In a molar ratio of 1:2 to 2: 1.
4. The method of claim 2, wherein R is naphthalene imide1-NH2And R2-NH2The total molar amount of the 1,4,5, 8-naphthalene tetracarboxylic anhydride is 1 to 5 times of the molar amount of the 1,4,5, 8-naphthalene tetracarboxylic anhydride.
5. The method of claim 2, wherein the reaction is carried out at a temperature of 90 to 150 ℃ for 12 to 48 hours.
6. The method of claim 2, wherein the reaction is completed and the product is cooled, poured into water, filtered and purified by column chromatography.
7. The method of claim 6, wherein the column chromatography is silica gel column, and the mobile phase is dichloromethane and/or chloroform.
8. A naphthalimide-based photochromic material, wherein the raw material for producing the naphthalimide-based photochromic material comprises the naphthalimide-based compound according to claim 1.
9. Use of the naphthalimide compound according to claim 1 for the preparation of photochromic materials.
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| US10656515B2 (en) * | 2015-08-11 | 2020-05-19 | Council Of Scientific & Industrial Research | Photochromic metal organic frameworks for inkless and erasable printing |
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| EP0031956A1 (en) * | 1980-01-04 | 1981-07-15 | Agfa-Gevaert AG | Photosensitive recording material |
| WO2020043895A1 (en) * | 2018-08-30 | 2020-03-05 | The University Court Of The University Of Glasgow | Photochromic and electrochromic compounds |
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